Hydrochloric Acid → 7750-45-0

HRID 1384450Notes

Reaction equation

HRID 1384450 reaction equation
[C:1]([O:5][C:6](=[O:31])[C@H:7]([CH2:16][CH2:17][CH2:18][CH2:19][NH:20]C(OCC1C=CC=CC=1)=O)[NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])([CH3:4])([CH3:3])[CH3:2].[ClH:32]>CCO.[Pd]>[ClH:32].[C:1]([O:5][C:6](=[O:31])[C@H:7]([CH2:16][CH2:17][CH2:18][CH2:19][NH2:20])[NH:8][C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 10526923Nalpha-BOC-Nepsilon-CBZ-L-Lysine tert-Butyl Ester

Product 1

HCID 513584377750-45-0Yield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Nα,-BOC-Nε-CBZ-L-lysine tert-butyl ester (3) (34.51 g, 79.15 mmol) was dissolved in a mixture of 300 ml absolute EtOH and 1 N HCl (88 ml). Prior to the introduction of H2 gas, 10% Pd—C (2.95 g) was added. After 7 hours, additional catalyst (1.0 g) was added. After 5 hours, the black suspension was filtered through a bed of Celite and washed with EtOH. The filtrate was concentrated, and the residue was dried under high vacuum to give the Nα-BOC-L-lysine tert-butyl ester as its hydrochloride salt (4) (26.59 g, 99%). 1H NMR (CD3OD) δ3.95 (dd, 1 H, J=8.8, 5.0), 2.93 (t, 2 H, J=7.7), 1.84-1.60 (m, 6 H), 1.45 (s, 9 H), 1.43 (s, 9 H); 13C NMR (CD3OD) δ173.5, 158.2, 82.7, 80.5, 79.5, 55.5, 40.6, 32.1, 28.7, 28.3, 23.9. HRMS m/z calcd. for C15H31N2O4 303.2284, found 303.2272. [α]26D−10.1°(c=1.00, CH3OH).

Workup

  1. waitAfter 5 hours
  2. filtrationthe black suspension was filtered through a bed of Celite
  3. washwashed with EtOH
  4. concentrationThe filtrate was concentrated
  5. customthe residue was dried under high vacuum

Sources & evidence

ORD record
ord-4e2709015bc841f699755a5b17528617
Source dataset
uspto-grants-2001_07
Patent number
US06258931B1

Reaction notes

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